The present invention is a method for manufacturing industrially important compounds containing (hydrocarbonoxy)silyl groups with good efficiency using hydrido (hydrocarbonoxy) silane compounds and aliphatic unsaturated organic compounds as source materials.
Hydrido (hydrocarbonoxy)silane compounds, as typified by SiH-functional alkoxysilanes, are important raw materials of modified silicones and are also used as crosslinking agents, for example, in the surface modification of various types of substrates and in curing reactions of polymers.
Methods for manufacturing compounds containing (hydrocarbonoxy)silyl groups, as typified by alkoxysilyl groups, can be divided into the following two main categories:
1. Methods in which a hydrosilylation reaction is caused to take place between aliphatic unsaturated organic compounds and hydridochlorosilane compounds, and in which an alcohol decomposition of the chlorine atoms bonded to the silicon atoms is further performed. PA1 2. Methods in which a hydrosilylation reaction is caused to take place between aliphatic unsaturated organic compounds and hydridoalkoxysilane compounds. PA1 (a) Carboxylic acids, with no particular restrictions on these acids, as long as the acids have carboxyl groups. Examples of such acids include saturated carboxylic acids, unsaturated carboxylic acids, monocarboxylic acids and dicarboxylic acids. The portions of these carboxylic acids other than the carboxyl groups are ordinarily selected from the group consisting of saturated or unsaturated aliphatic hydrocarbon groups, aromatic hydrocarbon groups, halogenated hydrocarbon groups and hydrogen atoms. Furthermore, substituent groups such as amino groups, silyl groups, or hydroxyl groups may also be bonded to these hydrocarbon groups.
Of these methods, the second method involve a simple process and allow the manufacture of products containing few ionic impurities. However, in order to perform the second method effectively, the use of a catalyst which has superior activity and selectivity for the hydrosilylation reaction is indispensable.
In regard to hydrosilylation reactions, it is known that certain types of compounds prevent a loss of activity by the catalyst and increase the reaction activity. However, such characteristics are limited to chlorosilane compounds and siloxane compounds. Furthermore, in the case of hydrosilylation reactions, it is often necessary to add oxygen to the reaction atmosphere in order to realize and maintain the catalytic activity and accordingly there is a danger of ignition and explosion.
The object of the present invention is to provide a novel method for making compounds containing (hydrocarbonoxy)silyl groups by means of a hydrosilylation reaction using hydrido (hydrocarbonoxy)silane compounds. Specifically, the present invention makes it possible to make compounds containing (hydrocarbonoxy)silyl groups by increasing the activity of the platinum or platinum compound catalyst in a hydrosilylation reaction between a hydrido (hydrocarbonoxy)silane compound and an aliphatic unsaturated organic compound, and preventing any drop in this activity so that hydrosilylation can be performed efficiently and economically.
Furthermore, the activity of the aforementioned platinum catalyst is increased, and the duration of this activity is improved, by the present method. As a result, the hydrosilylation reaction can be performed at a low oxygen partial pressure or in an inert atmosphere so that the danger of ignition or explosion during the hydrosilylation reaction is reduced.